Patent GB-929397-A (GB)
Title: Improvements in or relating to polyepoxide/bitumen compositions
IPC: H01R13/625
Filed: 1960-05-09
Abstract: A composition suitable for coating concrete, asphalt, wood or metal, especially in the form of roads or runways comprises (i) at least one polyepoxide having more than one vicinal epoxy group in the molecule; (ii) a bituminous material; and (iii) at least one compound of the formula:-  <FORM:0929397/IV(a)/1> in which X is an alkylene radical that can be substituted by at least one hydrocarbon group; R1 is a hydrocarbon radical containing at least 13 C that can be substituted by at least one halogen atom or hydroxy or oxo group; and R is H or an amino- or hydrocarbonamidoalkyl radical, where the hydrocarbon group of the hydrocarbonamide residue contains at least 13 C and can be substituted by at least one halogen atom or hydroxy or oxo group, and where the alkyl radical can have at least one chain of carbon atoms interrupted by a secondary amino group and can be substituted by at least one hydrocarbon group.  Long lists of suitable compounds are given, the following being exemplified:-(i) epichlorhydrin/bisphenol A, with, in Examples 10, 11, and 12, the polyglycidyl ester of trimerized linoleic acid; (ii) asphalts, petroleum distillates, coal tars and residual fuel oils; (iii) the reaction product of soyabean oil or tall oil fatty acids with ethylene diamine bottoms, of linoleic acid with ethylene diamine or diethylene triamine, of oleic acid with 1,4-butane diamine or diethylene triamine, or of a mixture of stearic and linoleic acids, with ethylene diamine.  Optional additives specified are:- hydrocarbon polymers, e.g. polyisoprene or polybutadiene; halohydrocarbon polymers, e.g. neoprene (a polychloroprene); inert particles, e.g. sand, rocks, shells, quartz, and fused alumina; conventional epoxy curing agents, e.g. a C12 monoamine, diethylene triamine, tetraethylene pentamine, the acids or amines used to make (iii), and polybasic acid anhydrides; solvents, e.g. xylene, benzene, fuel oil, gasoline, "Cellosolve" (Registered Trade Mark) or kerosine; reactive diluents, e.g. acryloor proprio-nitriles, butyl or allyl glycidyl ethers, and the glycidyl ethers of polyhydric alcohols.ALSO:Aza compounds of the formula:-<FORM:0929397/IV(a)/1> where X is an alkylene radical that can be substituted by at least one hydrocarbon group; R1 is a hydrocarbon radical containing at least 13C that can be substituted by at least one halogen atom or hydroxy or oxo group; and R is a hydrogen atom or an amino- or hydrocarbonamido-alkyl radical, wherein the hydrocarbon group of the hydrocarbonamido residue contains at least 13C and can be substituted by at least one halogen atom or hydroxy or oxo group, and wherein the alkyl residue can have at least one chain of carbon atoms interrupted by a secondary amino group and can be substituted by at least one hydrocarbon group, are prepared by reacting one or more long chain carboxylic acids with one or more polyamines, preferably at 100-250 DEG C. for 2-16 hours.  Acids specified are palmitic, pentadecanoic, 4-ketomyristic, 8,10-dibromostearic, margaric, stearic, x\s3-chlorostearic, linoleic, oleic, 8,10-dihydroxy-stearic, arachidic, behenic, 3-ketobehenic, lignoceric, cerotic, melissic, and mixtures thereof, e.g. those derived from standard bone tallow, yellow grease, fatty acid residue, tall oil, and soyabean oil.  The polyamines are preferably alkylene polyamines of the formula <FORM:0929397/IV(a)/2> where R is alkylene, or hydrocarbon substituted alkylene and n is an integer; 3-isopropylamino-propylamine is also mentioned.  The water of reaction may be removed under reduced pressure or by entraining with benzene, toluene or xylene.  In an example, ethylene diamine bottoms is reacted with tall oil fatty acids to give a mixture of <FORM:0929397/IV(a)/3> and <FORM:0929397/IV(a)/4> There is also described the preparation of a diglycidyl ether of bisphenol A by the reaction of bisphenol A and epichlorhydrin.ALSO:A composition suitable for coating concrete, asphalt, wood or metal, especially in the form of roads or runways comprises (i) at least one polyepoxide having more than one vicinal epoxy group in the molecule; (ii) a bituminous material; and (iii) at least one compound of the formula:- <FORM:0929397/V/1> in which X is an alkylene radical that can be substituted by at least one hydrocarbon group; R1 is a hydrocarbon radical containing at least 13 C that can be substituted by at least one halogen atom or hydroxy or oxo group; and R is H or an amino- or hydro carbonamidoalkyl radical, where the hydrocarbon group of the hydrocarbonamide residue contains at least 13C and can be substituted by at least one halogen atom or hydroxy or oxo group, p  and where the alkyl radical can have at least one chain of carbon atoms interrupted by a secondary amino group and can be substituted by at least one hydrocarbon group.  Long lists of suitable compounds are given, the following being exemplified;- (i) epichlorhydrin/bisphenol A, with in Ex, 10, 11 and 12, the polyglycidyl ester of trimerized linoleic acid; (ii) asphalts, petroleum distillates, coal tars and residual fuel oils; (iii) the reaction product of soyabean oil or tall oil fatty acids with alkylene diamine bottoms, of linoleic acid with ethylene diamine or diethylene triamine, of oleic acid with 1, 4-butane diamine or diethylene triamine, or of a mixture of stearic and linoleic acids with ethylene dimiane.  Optional additives specified are:-hydrocarbon polymers, e.g. polyisoprene or polybutadiene; halohydrocarbon polymers, e.g. Neoprene (a polychloroprene); inert particles, e.g. with ethylene diamine. Optional additives specified are:-hydrocarbon polymers, e.g. polyisoprene or polybutadiene; halohydrocarbon polymers, e.g. Neoprene a polychloroprene) ; inert particles, e.g. sand, rocks, shells, quartz, and fused alumina; conventional epoxy curing agents e.g. a C12 monoamine, diethylene triamine, tetraethylene pentamine, the acids or amines used to make (iii), and polybasic acid anhydrides; solvents, e.g. xyene, benzene, fuel oil, gasoline, "Cellosolve" (Registered Trade Mark) or kerosine; reactive diluents, e.g. acrylo- or proprionitriles, butyl or allyl glycidyl ethers, and the glycidyl ethers of polyhydric alcohols.